Cyclic acetals



lent alcohol, such as 1.2-dihydroiiyethane, a

Patented Dec. 22, 1931 ANGELO xivorm, or 'BERLINJAND ALBERT wnrssn vnonm ASSIGNORS TO wmrnnor CHEMICAL COMPANY, Inc, or

PORATION on NEW YORK v or norsnarr, ennmanv, NEW YORK, N. Y., A concYcmc AcErAIis No Drawing. Application filed February 12, 1930, Serial No. 427,;Q8Z, andin Germany February 2 Our present invention relates to new odoriferous substances and more particularly to hy-des.

We have found that the hitherto unknown cyclic acetals of the general formula in which R represents an araliphatic hydrocarbon radical of the benzene series and R stands for an aliphatic hydrocarbon radical have generally apronounced intensive and very agreeable odor, so that they are very useful in the manufacture of perfumes in contradistinction to the known cyclic acetals deriving from aliphatic .aldehydes or benzald'ehyde and a bivalent alcohol and possessing only a faint agreeable or even disagreeable odor.

Our newproducts are obtainable according to the known methods for preparing acetals when starting from an araliphatic aldehyde, such as, for instance, phenylacetaldehyde, hydratropic aldehyde, hydrocinnamic aldehyde, cinnamic aldehyde and from a bivacyclic acetals deriving from araliphatic aldedihy-droxybutane, a dihydroxypentan'e, and

so on. The new acetals are in the purified state at ordinary temperature colorless liquids, partly somewhat viscous. i

The following examples serve to illustrate our invention:

Example 1. parts or" 1-oX0-2-phenylethane (phenylacetaldehyde) are introduced drop by drop in the course of 4 hours at 15 (3. into 500 to 600 parts of 1.2-dihydroxyethane containing 1 per cent of gaseous hydrogen chloride. Formation and separation of water occurs. After having stirred for some time, the reaction product is washed or directly distilled in a vacuum while recovering unchanged dihydroxyethane. to parts of an 'acetal are obtained boiling at be.- tween 115 C. and 120 C. under 12 of fresh roses.

ethane (p y ta hy l a cau d react with 500 parts of 1.2-dihydro rybutane according to Example 1 and there are pressure. of roses.

Ewample 2. 100 parts of 1- oXo-2 -phenylethane (phenylaceta'ldehyde) are caused to act upon 500 parts of dihydroxypropane as described in Example 1 and thereare ob; tamed parts of an acetal boiling at 100 1 11 a eryagr e b fies edpr C. under 5 pressure and having an odor Emmz le 3:1

0 tained 14 0 to parts of an acetal boiling at between 107 C. and 110 C. under 5 mm. P es ure and hav ng n d of hyac t Example 4.-100 partsof 1-,o o-2 -phenyl han (ph lac t h ar e l s to act upon 500parts of 1.3-dihydro2gybutane according to Example 1 and there are obt i e 15. ar of an e al b il n a 1 3 C. to 135 under 14 mm. pressure having an odor of hyacinths.

Eazample 5.l00 parts of l-oxo-Q-phenylethane (phenylacetaldehyde) are causedto act upon 100 parts of 2.4-dihydrony-4-methylpentane according to Example 1. On distilling in a vacuum there are obtained besides water and 260 parts of unchanged QA dihy droxyle-metliylpeiitane 200 parts of an acetal boiling at between 110 C. and 115 C. under 5 mm. pressure and having a very agreeable and characteristic odor of mignonette.

E am e 6-., 0 Part O lonhy Q- methyiiathane (hydratropic, aldehyde) are caused to act upon 300 parts of LQ-dihydroXyethane according to Example 1. 7 There are obtained 1 10 parts of an acetal at 100 C. to 108 C. under 5 mm. pressure,- having,

a n n g ee l r k ea th a d us rooms Example 7.100 parts of 1-oXo-2-phenyl- EZ-methylethane (hydratropic aldehyde) are caused to react with 400 parts of 2. .l-dihydres -tme p ntam in he m nn escribed in Example 1. There are obtained 150 parts of an acetal boiling at between 115 C. and 120 C. under 5 mm. pressure, having a herbaceous odor of mignonette.

Example 8.100 parts of 1-oXo-3-phenylpropane (hydrocinnamic aldehyde) are caused to act upon 300 parts of 1.2-dihydroxyethane according to Example 1. There are obtained 110 parts of an acetal boiling at between 115 C. and 120 C. under 5 to 6 mm. pressure and having an odor like flowers and fruits.

Ewample .9.100 parts of 1-oXo-3-phenylpropane (hydrocinnamic aldehyde) are caused to act upon 100 parts of 2.4-dihydroxy- 4E-methylpentane according to Example 1. There are obtained 130 parts of an acetal boiling at 130 C. under 5 mm. pressure and having an odor like flowers and fruits.

E wample 10.100 parts of 1-oXo-3-phenylpropen-2 (cinnamic aldehyde) are caused to act upon 300 parts of 1.2-dihydroxyethane according to Example 1. There are obtained 105 parts of an acetal boiling at between 140 C. and 1 15 C. under 8 mm. pressure and having an agreeable odor resembling that of oil of cinnamon.

Example 11.-100 parts of 1-oXo-3-phenylpropen (cinnamic aldehyde) are caused to act upon 400 parts of QAC-dihydrOXy- L-methyL pentane according to Example 1. There are obtained 160 parts of an acetal boiling at between 155 C. and 160 C. under 5 mm. pressure. It has a soft natural cinnamic odor.

The new cyclic acetals may be worked up to perfumes in the known manner by diluting them with suitable solvents and by adding, if desired, other natural or artificial odoriferous substances.

Numerous other embodiments are possible and we contemplate as included within our invention all such modifications and equivalents as fall within the scope of the appended claims. Other processes known in the art of manufacturing acetals may be used to prepare our new products in an analogous manner.

What we claim is 1. As new products the cyclic acetals of the general formula in which R is an araliphatic hydrocarbon radical of the benzene series and R stands for a pentane hydrocarbon radical, said acetals being at ordinary temperature in the purified state colorless liquids having an intensive and very agreeable odor.

3. As new products the cyclic acetals of the general formula in which R stands for an aliphatic hydrocarbon radical, said acetals being at ordinary temperature in the purified state colorless liquids having an intensive and very agreeable odor. V

4. As new products the cyclic acetals of the general formula being in the purified state a colorless liquid boiling at about 110 C. to about 150 C. under 5 mm. pressure and having a very agreeable and characteristic odor of mignonette.

6. A perfume containing a cyclic acetal of the general formula in which It represents an araliphatic hydrocarbon radical of the benzene series and It stands for an aliphatic hydrocarbon radical.

7. A perfume containing a cyclic acetal of the general formula in which R is an araliphatic hydrocarbon 1 radical of the benzene series and R stands for a pentane hydrocarbon radical.

8. A perfume containing a cyclic acetal of the general formula in which R stands for an aliphatic hydrocarbon radical.

9. A perfume containing a cyclic acetal of the general formula in which R stands for a pentane hydrocarbon radical.

10. A perfume containing the cyclic acetal of the formula OH: CH:

comprises acting alcohol with an benzene serles 1n 11. The process which upon a bivalent aliphatic araliphatic aldehyde of the l the presence of a condensing agent.

12. The process which comprises acting upon a bivalent aliphatic alcohol with an araliphatic aldehyde of the benzene series in the presence of hydrochloric acid.

In testimony whereof, We aflix our signa- 

